Skip to content

MAKE EVERY MOMENT A MILESTONE! Enjoy free US shipping on orders over $150

Search

Account Log in Cart

Menu

New
Back to School

Collegiate

Swimwear
Girls
Back to School

Collegiate
Boys
Back to School

Collegiate
Baby
Classic Knits

Monogram Bloomers
Back to School
Collections
Back to School

Collegiate
Sale

Home
All Boys

All Boys

(864 products)

Discover timeless elegance for your little gentleman! Our collection features adorable smocked bubbles, jon jons, and coordinating outfits perfect for every occasion. From heirloom-quality pieces to everyday essentials, find expertly crafted boys clothing with customizable monogram options that create cherished keepsakes for years to come.

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

FiltersFilter & Sort

Applied Filters

Clear all

Gender

Boys (864)
Girls (146)
Women (3)

Clear

Features

Appliqué (80)
Embroidered (141)
Smocked (147)
Monogram (562)

Clear

Style

Bubbles (83)
Jon Jons (99)
Longalls (23)
Outerwear (17)
Pajamas (72)
Pant Sets (19)
Pants (27)
Rompers (44)
Shirts (234)
Shoes (5)
Short Sets (77)
Shorts (22)
Swimwear (19)
Backpacks (3)
Bags (21)
Baskets (2)
Belts (3)
Bibs (4)
Birthday (3)
Blankets (5)
Books (17)
Bracelets (2)
Hats (17)
Layette (8)
Lunch Boxes (4)
Seasonal (2)
Socks (8)
Sunglasses (2)
Towels (2)
Toys (20)

Clear

Size

Preemie (14)
Newborn (42)
3M (294)
6M (269)
9M (297)
12M (453)
18M (392)
24M (387)
2T (482)
3T (465)
4T (332)
5 (333)
6 (322)
7 (310)
8 (262)
10 (262)
12+ (42)
XS (27)
S (33)
M (33)
L (24)
XL (21)

Clear

Color

Blue (535)
Purple (31)
Pink (93)
Red (120)
Orange (29)
Yellow (24)
Green (155)
White (262)
Tan (25)
Brown (13)
Gray (7)
Black (12)
Metallic (5)
Multi (72)

Clear

Shoe Size

Baby 3 (4)
Baby 4 (4)
Child 5 (5)
Child 6 (3)
Child 7 (4)
Child 8 (4)
Child 9 (5)
Child 10 (5)
Child 11 (5)
Child 12 (5)
Child 13 (5)

Clear

Brand

Angel Dear (1)
Apple Of My Isla (6)
Beyond Creations (1)
Bunnies by the Bay (1)
Classic Whimsy (654)
Floafers (1)
Jefferies Socks (8)
Magnolia Baby (6)
Mint (24)
Mud Pie (35)
Penguin Random House (10)
Petit Ami (2)
Southern Sunshine (107)
Sun-San (4)
Vive La Fete (1)
Wee Ones (1)
Zsa Zsa & Lolli (2)

Clear

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

New

White Layette Gown with Blue Trim

$42.84

White/Blue
New

White Layette Gown

$42.84

White
New

Light Blue Corduroy Collared Bubble

$49.98

Light Blue
New

Light Blue Corduroy Collared Pant Set

$49.98

Light Blue
New

Green Corduroy Collared Pant Set

$49.98

Green
New

Light Blue Corduroy Pants

$49.98
New

Light Blue Corduroy Longall

$49.98

Light Blue
New

Tractor Applique Green Jogger Set

$49.98
New

Airplane & Clouds Pajamas

$47.12
New

Airplane & Clouds Polo Romper

$42.84
New

Airplane & Clouds Polo

$41.41
New

Pirate Ship Pajamas

$47.12
New

Pirate Ship Print Polo Romper

$42.84
New

Pirate Ship Polo

$41.41
Little Bro - Little Sis Plush Bears

$35.71

Blue Pink
My First Farm Plush Set

$57.14
New

Birthday Balloon Polo Romper

$42.84

Birthday Balloon
Sale

Easter Plush Bunny

$22.86 ~~$34.28~~

Tan Ivory
New

Birthday Balloon Pajamas

$47.12
Musical Bear Cuddle Pals

$38.57

Blue Pink
My Favorite Sports Bag Plush Set

$54.28
My First Tool Box Plush Set

$54.28
Big Brother - Big Sister Sound Book

$31.43

Blue Pink
New

Colorful Crayon Polo Romper

$42.84

Colorful Crayon
Sale

Seashell Smocked Blue Gingham Short Set

$49.98 ~~$64.27~~
New

Texas Embroidered Performance Polo

$64.27
Texas Embroidered Jon Jon

$69.98
New

Glossy Wipeable Train Case

$45.71

Navy Stripe Pink Stripe Baby Blue Stripe
New

Glossy Wipeable Snack Square

$25.71

Pink Stripe Baby Blue Stripe Navy Stripe
Glossy Wipeable Two-Piece Travel Jet-Set

$48.57

Pink Bungalow Blue Bungalow Superstar Heart
Glossy Wipeable Jumbo Big Mama Tote

$88.56

Pink Bungalow Blue Bungalow Pink Gingham Baby Blue Gingham Flamingo Electric Blue
New

Red Apple Smocked Blue Gingham Short Set

$57.12
New

Red Plaid Short

$28.55
New

School Bus Smocked Royal Gingham Jon Jon

$55.69
New

Green V-Neck Sweater

$42.84
New

Oxford Plaid Longall

$49.98
New

Galloway Plaid Button Down Shirt

$39.98
Colorful Crayon Smocked Blue Gingham Short Set

$64.27
New

Bright School Year Smocked Red Gingham Short Set

$64.27
New

Bright School Year Smocked Red Gingham Jon Jon

$64.27
New

School Ready Smocked Blue Plaid Short Set

$64.27
New

School Ready Smocked Blue Plaid Jon Jon

$64.27
New

School Days Smocked Navy Plaid Jon Jon

$64.27
Sale

White Short Sleeve Button Down Shirt

$28.55 ~~$39.98~~
New

Firehouse Dog Red Stripe Short Sleeve Pocket Shirt

$35.70

Firehouse Dog Red
Sale

Pirate Ship Light Blue Stripe Short Sleeve Pocket Shirt

$28.55 ~~$35.70~~

Pirate Ship Light Blue
New

Truck Blue Stripe Short Sleeve Pocket Shirt

$35.70

Truck Blue
New

Truck Blue Stripe Polo Romper

$42.84

Truck Blue

Previous
Page 3 / 18
1
2
3
4
5
…
18
Next

Shop Collection Favorites!

Beach

Shop
Collegiate

Shop
Back to School

Shop

Your cart

Your cart is empty

Subtotal:$0.00 CAD

Loading...

Facebook
Instagram
TikTok
Pinterest

Customer Care

Contact Us
FAQ
Rewards
Shipping
Size Guide
Returns

Shop

New
Girls
Boys
Baby
Collections
Sale

Newsletter

Sign up for exclusive offers, original stories, events and more.

Email

© 2026 Classic Whimsy.

About Us
Blog
Safety & Recall